1,1'-(Diazomethylene)bis(benzene) → HCID 131709936, compound

HRID 1580501Notes

Reaction equation

HRID 1580501 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:27](=[O:28])[N:13]3[CH:14]([C:24]([OH:26])=[O:25])[C:15]([CH2:18][C:19]4[S:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]1([C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N+]=[N-])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.C(OCC)(=O)C>[C:29]1([CH:35]([O:25][C:24]([CH:14]2[N:13]3[C:27](=[O:28])[C@@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C@H:12]3[S:17][CH:16]=[C:15]2[CH2:18][C:19]2[S:23][CH:22]=[CH:21][CH:20]=2)=[O:26])[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 131709937HCID 131709937, compound

Product 1

HCID 131709936HCID 131709936, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7β-phenylacetylamino-3-(2-thenyl)-ceph-2-em-4ξ-carboxylic acid in 150 ml of methanol is diluted with 200 ml of ethyl acetate, then treated with 9.70 g of diphenyldiazomethane in 20 ml of ethyl acetate. The reaction mixture is stirred at room temperature for 1 hour and evaporated to dryness under reduced pressure. The residue is crystallised from ethyl acetate and chromatographed on 400 g of silica gel. Elution with ethyl acetate yields the 7β-phenylacetylamino-3-(2-thenyl)-ceph-2-em-4ξ-carboxylic acid diphenylmethylester, which after recrystallisation from ethyl acetate melts at 166°-167°; [α]D20 = + 359° ± 2° (c = 0.490 in 95% ethanol); thin-layer chromatogram (silica gel): Rf = 0.73 (system: toluene/ethyl acetate 1:1) and Rf = 0.56 (system: toluene/acetone 4:1); ultraviolet absorption spectrum (in 95% alkanol): strong terminal absorption; infrared absorption spectrum (in mineral oil); characteristic bands at 2,97μ, 5,62μ, 5,75μ, 6,03μ and 6,54μ.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue is crystallised from ethyl acetate
  3. customchromatographed on 400 g of silica gel
  4. washElution with ethyl acetate

Sources & evidence

ORD record
ord-5e924ce24931418d9002cb1f062c6b3d
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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